Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones
| Autor: | Yu-Mei Hu, Bin Tan, Yong-Bin Wang, Sheng-Cai Zheng |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Quantitative Biology::Biomolecules
Multidisciplinary 010405 organic chemistry Chemistry High Energy Physics::Lattice Science High Energy Physics::Phenomenology Enantioselective synthesis General Physics and Astronomy Total synthesis General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry General Biochemistry Genetics and Molecular Biology Article 0104 chemical sciences Catalysis Yield (chemistry) Brønsted–Lowry acid–base theory Axial symmetry Bond cleavage |
| Zdroj: | Nature Communications, Vol 8, Iss 1, Pp 1-9 (2017) Nature Communications |
| ISSN: | 2041-1723 |
| Popis: | The axially chiral arylquinazolinone acts as a privileged structural scaffold, which is present in a large number of natural products and biologically active compounds as well as in chiral ligands. However, a direct catalytic enantioselective approach to access optically pure arylquinazolinones has been underexplored. Here we show a general and efficient approach to access enantiomerically pure arylquinazolinones in one-pot fashion catalysed by chiral phosphoric acids. A variety of axially chiral arylquinazolinones were obtained in high yields with good to excellent enantioselectivities under mild condition. Furthermore, we disclosed a method for atroposelective synthesis of alkyl-substituted arylquinazolinones involving Brønsted acid-catalysed carbon–carbon bond cleavage strategy. Finally, the asymmetric total synthesis of eupolyphagin bearing a cyclic arylquinazolinone skeleton was accomplished with an overall yield of 32% in six steps by utilizing the aforementioned methodology. Axially chiral arylquinazolinones are structural motifs in several natural products and can also act as chiral ligands. Here, the authors show a chiral phosphoric acid-catalysed strategy to access enantiomerically pure arylquinazolinones by efficient transfer of central chirality into axial chirality. |
| Databáze: | OpenAIRE |
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